22927-03-3

Upstream product

• 108-88-3 toluene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1052721-72-8 N-propyl(1-(4-methoxyphenyl)vinyl)sulfane 
• 6921-34-2 benzylmagnesium chloride 
• 696-62-8 para-iodoanisole 
• 583-04-0 vinyl benzoate 
• 98-80-6 phenylboronic acid 
• 300-57-2 allylbenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 100-44-7 benzyl chloride 

Downstream Products

• 5912-82-3 (E)-2-(4-methoxyphenyl)-1-phenylpropene 
• 1380439-41-7 (Z)-2-(4-methoxyphenyl)-1-phenylprop-1-ene 
• 86516-51-0 1-(4-methoxyphenyl)-2-tosylethanone 

Relevant academic research and scientific papers

Reductive hydrobenzylation of terminal alkynesviaphotoredox and nickel dual catalysis

A photoredox/nickel dual catalyzed reductive hydrobenzylation of alkynes and benzyl chlorides by employing alkyl amines as a stoichiometric reductant is described. This synergistic protocol proceedsviaMarkovnikov-selective migratory insertion of an alkyne into nickel hydride, followed by cross-coupling with benzyl chloride, providing facile access to important 1,1-disubstituted olefins. This reaction enables the generation of nickel hydride by utilizing readily available alkyl amines as the hydrogen source. The mild conditions are compatible with a wide range of aryl and alkyl alkynes as well as chlorides.

Intermolecular [4 + 2] process of N-acyliminium ions with simple olefins for construction of functional substituted-1,3-oxazinan-2-ones

An efficient approach to functionalized 4,6-disubstituted-and 4,6,6-trisubstituted-1,3-oxazinan-2-ones skeleton has been developed through the reaction of semicyclic N,O-acetals 4a and 4b with 1,1-disubstituted ethylenes 5 or 8. As a result of such a [4 +

Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes

Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkenes can serve as an alternative approach to trisubstituted alkenes, but it remains underdeveloped owing to issues relating to reaction efficiency and stereoselectivity. Here we show that a novel cobalt catalyst can overcome these challenges to provide an efficient and stereoselective access to a broad range of trisubstituted alkenes. This protocol is compatible with both mono- and dienes and exhibits a good functional group tolerance and scalability. Moreover, it has proven to be a useful tool to construct organic luminophores and a deuterated trisubstituted alkene. A preliminary study of the mechanism suggests that a cobalt-hydride pathway is involved in the reaction. The high stereoselectivity of the reaction is attributed to both a π-πstacking effect and the steric hindrance between substrate and catalyst.

Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives

We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.

Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions

Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.

Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: Efficient access to α-alkyl vinylarenes

Branched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TFA)2/dmphen (TFA = trifluoroacetate, dmphen = 2,9-dimethyl-1,10-phenanthroline) and proceed efficiently at 45-60 °C under 1 atm of O2 without requiring other additives. A broad array of functional groups, including aryl halide, allyl silane and carboxylic acids are tolerated.

Synthesis of 1,3-diarylpropenes through palladium-catalyzed mizoroki-heck and allyl cross-coupling reactions using hydrazones as ligands

The palladium-catalyzed synthesis of unsymmetrical 1,3-diarylpropenes from allyl esters through a Mizoroki-Heck-type reaction with aryl iodides followed by allyl cross-coupling with a variety of arylboronic acids was developed; the products are obtained in moderate to good yields by using a hydrazone-Pd(OAc) 2 system. The synthesis of unsymmetrical 1,3-diarylpropenes from allyl esters by a Mizoroki-Heck-type reaction followed by allyl cross-coupling with a variety of arylboronic acids was developed; the products were obtained in moderate to good yields by using a hydrazone-Pd(OAc)2 system. Copyright

Synthesis of 1,1-disubstituted olefins via catalytic alkyne hydrothiolation/Kumada cross-coupling

(Chemical Equation Presented) Using recently developed methodology for the regioselective formation of branched alkyl vinyl sulfides, we report a convenient route to 1,1-disubstituted olefins. We demonstrate that n-propanethiol successfully undergoes cata

Reaction of 2-Aryl-3-(N,N-dimethylamino)-1-propenes and Their Corresponding Quaternary Ammonium Salts with Organometallic Species and Reducing Agents

A series of 2-aryl-3-(N,N-dimethylamino)-1-propenes and their corresponding quaternary ammonium salts were reacted with a variety of organometallic species and reducing agents.The utility of such reactions for the preparation of α-substituted styrene derivatives is discussed.